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WO2012087602A3 - Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications - Google Patents

Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications Download PDF

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Publication number
WO2012087602A3
WO2012087602A3 PCT/US2011/064076 US2011064076W WO2012087602A3 WO 2012087602 A3 WO2012087602 A3 WO 2012087602A3 US 2011064076 W US2011064076 W US 2011064076W WO 2012087602 A3 WO2012087602 A3 WO 2012087602A3
Authority
WO
WIPO (PCT)
Prior art keywords
toughening particles
prepreg
partially soluble
epoxy resin
system containing
Prior art date
Application number
PCT/US2011/064076
Other languages
French (fr)
Other versions
WO2012087602A2 (en
Inventor
James Griffin
Mark Bonneau
Gordon EMMERSON
Original Assignee
Cytec Technology Corp.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cytec Technology Corp. filed Critical Cytec Technology Corp.
Priority to KR20137017061A priority Critical patent/KR20140007815A/en
Priority to EP11806038.3A priority patent/EP2655512B1/en
Priority to CA 2822578 priority patent/CA2822578A1/en
Priority to BR112013012882-8A priority patent/BR112013012882A2/en
Priority to JP2013546195A priority patent/JP5806332B2/en
Priority to CN2011800587354A priority patent/CN103249776A/en
Priority to AU2011349849A priority patent/AU2011349849B2/en
Publication of WO2012087602A2 publication Critical patent/WO2012087602A2/en
Publication of WO2012087602A3 publication Critical patent/WO2012087602A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
    • C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2481/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
    • C08J2481/06—Polysulfones; Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Reinforced Plastic Materials (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Resin compositions comprise an epoxy thermosetting resin; and at least two types of interlaminar toughening particles; wherein a first type of interlaminar toughening particles are insoluble in said epoxy thermosetting resin; wherein a second type of interlaminar toughening particles are partially soluble or swellable in said epoxy thermosetting resin. Prepregs and structural compounds contain these resin compositions, which are useful in the aerospace industry.
PCT/US2011/064076 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications WO2012087602A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
KR20137017061A KR20140007815A (en) 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications
EP11806038.3A EP2655512B1 (en) 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications
CA 2822578 CA2822578A1 (en) 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications
BR112013012882-8A BR112013012882A2 (en) 2010-12-22 2011-12-09 COMPOSITION, PREPREG, AND, COMPOSITE ARTICLE
JP2013546195A JP5806332B2 (en) 2010-12-22 2011-12-09 Epoxy resin systems containing insoluble and partially soluble or swellable reinforcing particles for use in prepreg and structural component applications
CN2011800587354A CN103249776A (en) 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications
AU2011349849A AU2011349849B2 (en) 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201061426383P 2010-12-22 2010-12-22
US61/426,383 2010-12-22

Publications (2)

Publication Number Publication Date
WO2012087602A2 WO2012087602A2 (en) 2012-06-28
WO2012087602A3 true WO2012087602A3 (en) 2012-11-08

Family

ID=45464853

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/064076 WO2012087602A2 (en) 2010-12-22 2011-12-09 Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications

Country Status (10)

Country Link
US (1) US20120164455A1 (en)
EP (2) EP2655512B1 (en)
JP (1) JP5806332B2 (en)
KR (1) KR20140007815A (en)
CN (1) CN103249776A (en)
AU (1) AU2011349849B2 (en)
BR (1) BR112013012882A2 (en)
CA (1) CA2822578A1 (en)
TW (1) TW201229126A (en)
WO (1) WO2012087602A2 (en)

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GB0606045D0 (en) * 2006-03-25 2006-05-03 Hexcel Composites Ltd A thermoplastic toughening material
US9567426B2 (en) * 2009-05-29 2017-02-14 Cytec Technology Corp. Engineered crosslinked thermoplastic particles for interlaminar toughening
KR101848114B1 (en) * 2010-12-17 2018-04-11 세키스이가가쿠 고교가부시키가이샤 Production method for polyamide acid particles, production method for polyimide particles, polyimide particles and bonding material for electronic component
CA2822578A1 (en) * 2010-12-22 2012-06-28 Cytec Technology Corp. Epoxy resin system containing insoluble and partially soluble or swellable toughening particles for use in prepreg and structural component applications
GB201222934D0 (en) * 2012-12-19 2013-01-30 Cytec Ind Inc Particle toughening for improving fracture toughness
EP2900739B1 (en) * 2012-12-21 2018-03-14 Cytec Engineered Materials Inc. Curable prepregs with surface openings
JP5736560B2 (en) * 2013-03-28 2015-06-17 福井県 Laminated molded body
WO2015011549A1 (en) * 2013-07-24 2015-01-29 Toray Industries, Inc. Fiber reinforced polymer composition with interlaminar hybridized tougheners
EP3086940A2 (en) 2013-12-23 2016-11-02 Cytec Industries Inc. Toughened composite materials and methods of manufacturing thereof
EP3087123B1 (en) * 2013-12-24 2020-07-15 Hexcel Composites Limited Improvements to matrix additives
JP6020734B2 (en) * 2014-06-30 2016-11-02 三菱レイヨン株式会社 Toe prepreg, composite material pressure vessel and manufacturing method thereof
US9587076B2 (en) * 2014-09-23 2017-03-07 The Boeing Company Polymer nanoparticles for controlling resin reaction rates
CA2968081C (en) * 2014-12-16 2022-11-22 Cytec Industries Inc. Epoxy-based resin composition for composite materials
US9758706B2 (en) 2015-07-31 2017-09-12 The Boeing Company Encapsulated catalyst for aerospace grade resin systems
US10106661B2 (en) 2016-06-22 2018-10-23 Hexcel Corporation Composite material with thermoplastic toughened novolac-based epoxy resin matrix
US10472474B2 (en) 2016-06-22 2019-11-12 Hexcel Corporation Semipreg with thermoplastic toughened novolac-based epoxy resin matrix
US10000615B1 (en) 2017-02-23 2018-06-19 Hexcel Corporation Retaining compressive strength of thermoplastic-toughened epoxy composites under hot and wet conditions
WO2018165073A1 (en) * 2017-03-07 2018-09-13 Cytec Industries Inc. Composite materials with structural and fire retardant capabilities
WO2019013716A1 (en) * 2017-07-12 2019-01-17 Kordsa Tekni̇k Teksti̇l Anoni̇m Şi̇rketi̇ Production method for a composite material made of resin formulation-impregnated fiber-reinforced intermediate
RU2676634C1 (en) * 2018-04-19 2019-01-09 Федеральное государственное унитарное предприятие "Всероссийский научно-исследовательский институт авиационных материалов" (ФГУП "ВИАМ") Prepreg based on adhesive binder of reduced flammability and fiberglass, carbon fiber on its basis
CN109467726A (en) * 2018-10-16 2019-03-15 厦门大学 Reinforcing method of interlaminar strength of fiber/resin matrix composite laminates using glass microbeads
US12227628B2 (en) 2018-12-21 2025-02-18 Cytec Industries Inc. Toughened composite materials capable of delamination propagation resistance
FR3128399A1 (en) * 2021-10-21 2023-04-28 Hexcel Reinforcements Process for manufacturing composite parts from a reinforcing material comprising a porous layer of a reactive thermoplastic polymer and a thermosetting resin
CN114181416A (en) * 2021-12-16 2022-03-15 中复神鹰(上海)科技有限公司 Production method for preparing interlayer toughened carbon fiber prepreg by one-step method

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US5082891A (en) * 1988-02-29 1992-01-21 Dow Corning Toray Silicone Co., Ltd. Curable resin composition containing dispersed particles of a cured silicone rubber
US6013730A (en) * 1994-06-07 2000-01-11 Fiberite, Inc. At least trifunctional epoxy resin reacted with solid rubber mixed with epoxy resin and curing agent
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US20100304118A1 (en) * 2009-05-29 2010-12-02 Cytec Technology Corp. Engineered crosslinked thermoplastic particles for interlaminar toughening

Also Published As

Publication number Publication date
JP2014501835A (en) 2014-01-23
AU2011349849B2 (en) 2014-03-27
AU2011349849A1 (en) 2013-04-04
WO2012087602A2 (en) 2012-06-28
US20120164455A1 (en) 2012-06-28
EP2655512B1 (en) 2016-11-23
CN103249776A (en) 2013-08-14
EP2655512A2 (en) 2013-10-30
CA2822578A1 (en) 2012-06-28
BR112013012882A2 (en) 2020-05-12
TW201229126A (en) 2012-07-16
EP3135718A1 (en) 2017-03-01
KR20140007815A (en) 2014-01-20
JP5806332B2 (en) 2015-11-10

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